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CS-W001157 4
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2-Acetyl-5-bromothiophene

  • CAS No. 5370-25-2

  • Cat. No. CS-W015388
  • Molecule weight205.07
  • Purity≥97%
  • MDL No.MFCD00014528

*For research and further manufacturing use only, not for direct human use.

2-Acetyl-5-bromothiophene|CS-W015388

Structure of 5370-25-2

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General Information

  • CAS No. 5370-25-2
  • Cat. No. CS-W015388
  • Purity ≥97%
  • MDL No. MFCD00014528
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅BrOS
  • Molecular Weight 205.07
  • Synonym(s) Ethanone, 1- (5-bromo-2-thienyl)-
  • SMILES CC(=O)C1=CC=C(Br)S1

Description

2-Acetyl-5-bromothiophene features a bromine substituent at the 5-position and an acetyl group at the 2-position, creating a bifunctional thiophene scaffold with enhanced reactivity. This electron-deficient heterocycle integrates readily into cross-coupling reactions and serves as a key intermediate in synthesizing functionalized thienyl compounds for materials science and medicinal chemistry applications.

Application

2-Acetyl-5-bromothiophene serves as a versatile building block in synthetic organic chemistry, enabling direct functionalization at the 5-position via palladium-catalyzed cross-coupling reactions. The bromine atom facilitates efficient C–C bond formation, while the acetyl group provides a handle for further transformations such as reduction or condensation. Its stability under standard reaction conditions and compatibility with diverse coupling partners make it well-suited for constructing complex heterocyclic scaffolds and advanced intermediates in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Arsenyan, Pavel; Paegle, Edgars; Belyakov, Sergey Tetrahedron Letters, 2010 , vol. 51, # 1 p. 205 - 208
  • Route2
    • null|null
      1003-09-4
    • null|null
      108-24-7
    • ~87%
    • In-stock
      2-Acetyl-5-bromothiophene|CS-W015388
      5370-25-2

    References

    • Potts, Kevin T.; Cipullo, Michael J.; Ralli, Philip; Theodoridis, George Journal of Organic Chemistry, 1982 , vol. 47, # 16 p. 3027 - 3038
  • Route3
    • null|null
      114774-05-9
    • ~94%
    • In-stock
      2-Acetyl-5-bromothiophene|CS-W015388
      5370-25-2

    References

    • Goda; Sato; Ihara; Hirayama Synthesis, 1992 , # 9 p. 849 - 851

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   2.7132
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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